Anthracene dye and process of making same.



. matters which dye vegetable fiber from analkaline hydrosulfite vat reddish brown to sri irns PATENT OFFFH it or Mimi-ram, GERMANY, ASSIGNOR TO sliniscnn' ANILIN & soniirlisani',

- or LUDWIGSHAFENONEHE-RHINE, GERMANY, A CORPORATION.

ANTHBACENE DYE nun .raocnss or MAKING SAME.

Patented May 18, 1909.

Application filed February 12, 1907. Serial No. 357,061.

l have discovered-that y heating anthrae cone, 'or a non-oxidized substitution com' pound thereof, with sulfur with, or without, the addition of a metal, or a metallic oxid, or hydroxid, or, salt, or a mixture of any "of these compounds, I can obtain new coloring olive-green shades of excellent fast'nessj By altering the temperature employed and also the metallic compound used, different shades and different intensities can .be obtained I, without the chief characteristics of the coloring matters being altered. For instance, by heating anthracene and sulfur together at a temperature of-about 250 C. a product is obtained which, with alkaline hydrosulfite,-

yields a brown vat and dyes cotton from this vat yellow-brown shades, while, if a-temperature of from 350-36() C. be em loyed the product'yields a bluevat and'cyes cotton olive-green shades which upon washing turn into brownish Olive. ried out in the presence of, for instance, alkali acetate, or carbonate, or hydrate, or sulfid, coloring matters can be obtained which yield duller shades. Among the .derivatives of anthracene which can be used according to this invention may be mentioned 9.l0.dichlor-anthracene, 2.9.'l0.trichlor anthrace'ne, dichlor-dibrom-anthracene, dichlor anthracene tetrabromid, 2 methylanthracene', and Z-anthramin. The two last mentioned compounds yield a reddenbrown'.

Anthraquinone, or any compound con taining the anthraquinone grouping that is' oxidized derivatives'of anthracene cannot be em )loycd "for this invention.

he new dyes which I wish to beunderstood as claiming generically are characterized by the following ro erties. .They are insoluble in water, in a ka ice, in dilute acids, and in the ordinary organic solvents, but are soluble in alkaline 'hydrosulfite, solutions yielding from brown to blue solutions which dye unmordanted cotton yielding from green-yellow to brown shades.

The followingexamples-willserve to illus "v If the reaction be car-- I I trateiurther the nature of' this invention and the method of carrying itinto practical eiiect,'but my invention is not confined to these examples; The parts are by weight.

Example 1: Heat together, at a temperature oftwo hundred and fifty (250) degrees centigrade, one hundred (100) parts of anthracene (containing from ninety-six (96), to

ninety-eight (98) per cent. of pure anthracene) andthree hundred (300) parts of sulfur, .until the evolution of sulfuretted hydrO-.

gen ceases. The product can beused directly for dyeing ,or it can be purified by removal of the excess of sulfur by means of sodium sulfid solution; The coloring matter is insoluble in water, in alkalies, in dilute acids, and in the ordinary organic solvents.

Example 2: Heat together, at a temperature offrom three hundred and fifty (350), to

three hundred and sixty (360), degrees. centigrade, one hundred (100) parts of anthracene (containing from ninety-six (96), to

ninety-eight (98), per cent of pure anthra-' acne) and three hundred (300) parts of sulfur, until the evolution of sulfuretted hydrogen ceases. The product can be Worked up as .described-inthe foregoing example 1.

EXampleiS: Heat together, at a temperature of from three hundred andfifty (3 50), to 1 three hundred and.siXty--(360), degrees centigrade, .one hundred (1.00).parts of anthracene (containing from ninety-six (96), to ninety-eight (98), per cent. of pure anthracene), three hundred (300) parts of sulfur and seventy-five parts of caustic soda. The product contains, beside the chief col- Orin ,matter, a small quantity of a bypro not which is soluble in Water, the solu tion being green, and which dyes cotton yielding much less intense shades thanthose yielded by the chief product. Itcan be ex- Now what I claim is; i

1. The processlof producing coloring mat. ter byheati'ng anthracene or acompound' ,tracted by means Of water, or sodium sulfid solution.

'or oXld, or salt,-or a metal, can be employed.

containing the anthracene grouping with sulfur.

2 The process of producing-coloring mat ter .by heating anthrac'ene or compound containing the anthracene grouping with sulfur in the presence of a metallic com pound.

3. The process of producing coloring matter by heating anthracene with sulfur in the presence of caustic soda.

4. The process of producing coloring mat ter by heating 9.10-dicl1loranthracene with.

brown to blue solutions which dye unmordanted cotton yielding from green-yellow to brown shades.

6. As a new article of manufacture the coloring matter which can be obtained from anthracene which coloring matter is insoluble in water, in alkalies, in dilute acids, and in the ordinary organic solvents, but is soluble in alkaline hydrosulfite solution yielding a blue vat which dyes unino'rdanted cotton greenisli olive shades.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MAX ISLER. Witnesses l T. LLOYD,

Hf W. HARRIs. 

